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Orange County?! Go out to some Dave & Buster's or an Applebee's and fuck some drunk sluts. Jeez... Orange County virgins... what's the world coming to.
Chicks have (almost) as many insecurities as you and me. The ones who slut themselves up before going out, even more so. Make them feel attractive and they will make you feel like you are getting your dick sucked.
Dumb sluts (and some smart ones) want to fuck you. I lived with the butt-ugliest roommate on earth. This fool fucked a new just-slightly-chubby chick every month. His secret? Having no shame.
You will strike out.
You will strike out with a chick who is too ugly to reject you.
THEN you will hit it.
THEN you will hit it with a chick who is too hot to get fucked by you.
Then you should jump off a bridge before your life stops getting better, because that will be the highlight of everything for quite some time to come.
Unless you can marry that chick. If you can marry her - go for it. Try not to let your friends or family or anyone in the world let her know that she is too good for you. Work really hard at this. Simultaneously, you should try to be as good as her. Landing a chick who is hotter (or funnier, or smarter or just otherwise better) than you will lead you to be a better person. Do you think JFK would have been president if he wasn't trying to live up to Jackie O's level of awesomeness, or Marilyn's level of hotness? (Would he have ever fucked Marilyn if he wasn't president because he was trying to keep up with Jackie O?)
It's an awesome cycle of getting better at life.
And it all starts with hitting on OK looking chicks at some lame-ass Orange County place. It doesn't start on Craigslist. On CL you will find chicks that have given up, like you. UnGive-up, my boy. Ungive-up and find chicks who have ungiven-up too, because they recognize how easy it is to achieve the task they're (and you're) trying to accomplish.